HCID 69508855, compound → HCID 11648628, compound

HRID 1593693Notes

Reaction equation

HRID 1593693 reaction equation
[CH3:1][O:2][CH2:3][C:4]#[C:5][C:6]1[CH:24]=[CH:23][C:9]([C:10]([NH:12][CH:13]2[C:18]([CH3:20])([CH3:19])[C@H:17]3[CH2:21][C@:14]2([CH3:22])[CH2:15][CH2:16]3)=[O:11])=[CH:8][C:7]=1[S:25]([N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)(=[O:27])=[O:26]>C(O)C.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:24]=[CH:23][C:9]([C:10]([NH:12][CH:13]2[C:18]([CH3:20])([CH3:19])[C@H:17]3[CH2:21][C@:14]2([CH3:22])[CH2:15][CH2:16]3)=[O:11])=[CH:8][C:7]=1[S:25]([N:28]1[CH2:29][CH2:30][O:31][CH2:32][CH2:33]1)(=[O:27])=[O:26]

Participants

4

Reactant 1

HCID 69508855HCID 69508855, compound

Product 1

HCID 11648628HCID 11648628, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(3-methoxy-prop-1-ynyl)-3-(morpholine-4-sulfonyl)-N-((1S,4R)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-benzamide 6.1 (220 mg, 0.46 mmol) in ethanol (20 mL) under nitrogen was added palladium on carbon (10 mg, 0.08 mmol). The reaction mixture was stirred under a hydrogen atmosphere for 2 hours then filtered through celite washing with ethanol. The solvent was evaporated and the residue was purified by silica gel chromatography using hexane/ethyl acetate (0-50%) to give the product 85 as a white solid (120 mg, 54% yield).

Workup

  1. filtrationthen filtered
  2. washthrough celite washing with ethanol
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7e36350ffa9d45e9b197b873b36b292f
Source dataset
uspto-grants-2007_11
Patent number
US07297796B2

Reaction notes

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